A dog.
Correct. A person sitting in a boat.
Correct. An upward pointing arrow with wings.
Correct! A person with a diamond head laying down.
No, not that one. This shape has a small diamond on the right side.
No, not that one. Try again.
No, not that one. This shape has a small diamond on the right side, touching the rest of the shape only at the corner.
No. This is a person with a diamond head that has fallen down with their head on the right.
No, not that one. This shape is long and horizontal.
NO. LONG HORIZONTAL SHAPE WITH A SMALL DIAMOND ON THE RIGHT END

Outcome: unsuccessful
Speaker comments: We were so close to greatness and then the bot imploded on the last shape. I have no idea what I was supposed to say to get it, it was an obvious shape with obvious distinctive features and the bot didn't get it, instead it had a little cry. So annoying.